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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-01-09 12:11:23 UTC
Update Date2019-07-23 07:12:46 UTC
HMDB IDHMDB0059720
Secondary Accession Numbers
  • HMDB59720
Metabolite Identification
Common NameMeta-Tyrosine
DescriptionMeta-Tyrosine, also known as L-m-tyr or m-tyrosine, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Meta-Tyrosine exudes out of the grass plant's roots and is then absorbed by neighbouring weed seedlings. The weed plants will either die or be stunted from the toxic acid. Meta-Tyrosine is a very strong basic compound (based on its pKa). Meta-Tyrosine, or M-Tyrosine for short, is a natural weed suppressant found in certain Fine fescue grass.
Structure
Data?1563865966
Synonyms
ValueSource
L-m-TyrChEBI
L-MTyrChEBI
m-TyrosineChEBI
(2S)-2-Azaniumyl-3-(3-hydroxyphenyl)propanoateHMDB
Meta-tyrosineChEBI
Chemical FormulaC9H11NO3
Average Molecular Weight181.1885
Monoisotopic Molecular Weight181.073893223
IUPAC Name(2S)-2-amino-3-(3-hydroxyphenyl)propanoic acid
Traditional Namemeta-tyrosine
CAS Registry NumberNot Available
SMILES
N[C@@H](CC1=CC=CC(O)=C1)C(O)=O
InChI Identifier
InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-2-1-3-7(11)4-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1
InChI KeyJZKXXXDKRQWDET-QMMMGPOBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • L-alpha-amino acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.13 g/LALOGPS
logP-2.3ALOGPS
logP-1.5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.1 m³·mol⁻¹ChemAxon
Polarizability18.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4j-3940000000-1f2530cb7cb335d32e40Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1890000000-b3a4950b74f78e8b1f1dSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4j-3940000000-1f2530cb7cb335d32e40Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1890000000-b3a4950b74f78e8b1f1dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-4900000000-591bb41c5e030f74ea66Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-5490000000-42f7ab53cd22e78f0445Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0900000000-b8767a6e66ce78d074feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-1823a449a868e6cb15d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-8900000000-41bb52abc360a513786fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-b18debca081bd463b44aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-8746c93314cbf487b162Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-7900000000-ff5570ce952504e52190Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03552
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5323512
KEGG Compound IDNot Available
BioCyc IDCPD-14541
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6950577
PDB IDMTY
ChEBI ID44303
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Engel J: Metatyrosine-induced reversal of the suppression of the conditioned avoidance response in reserpine-treated rats. Acta Pharmacol Toxicol (Copenh). 1971;30(3):278-88. [PubMed:4945487 ]
  2. CARLSSON A, LINDQVIST M: In-vivo decarboxylation of alpha-methyl DOPA and alpha-methyl metatyrosine. Acta Physiol Scand. 1962 Jan;54:87-94. [PubMed:13876658 ]
  3. Jagoda EM, Vaquero JJ, Seidel J, Green MV, Eckelman WC: Experiment assessment of mass effects in the rat: implications for small animal PET imaging. Nucl Med Biol. 2004 Aug;31(6):771-9. [PubMed:15246368 ]
  4. HESS SM, CONNAMACHER RH, OZAKI M, UDENFRIEND S: The effects of alpha-methyl-DOPA and alpha-methyl-metatyrosine on the metabolism of norepinephrine and serotonin in vivo. J Pharmacol Exp Ther. 1961 Nov;134:129-38. [PubMed:13907002 ]
  5. Shellenberger MK, Elder JT: Alterations in rabbit core temperature produced by alpha-methyl metatyrosine. Eur J Pharmacol. 1968 Jun;3(3):196-202. [PubMed:5673633 ]
  6. Hermand E, Leonardelli J, Tramu G: [Hypothalamic mechanism of the antiovulatory action of sulpiride]. Encephale. 1975;1(4):375-82. [PubMed:767098 ]
  7. ANDEN NE: ON THE MECHANISM OF NORADRENALINE DEPLETION BY ALPHA-METHYL METATYROSINE AND METARAMINOL. Acta Pharmacol Toxicol (Copenh). 1964;21:260-71. [PubMed:14209617 ]
  8. Magsino CH Jr, Hamouda W, Bapna V, Ghanim H, Abu-Reish IA, Aljada A, Dandona P: Nadolol inhibits reactive oxygen species generation by leukocytes and linoleic acid oxidation. Am J Cardiol. 2000 Aug 15;86(4):443-8. [PubMed:10946040 ]
  9. Kimura K, Kimura Y, Ohata K, Takagi H: Effects of several monoamine-related compounds on the reserpine-induced spikes recorded from the medial nucleus trapezoides in rabbits. Jpn J Pharmacol. 1978 Apr;28(2):317-27. [PubMed:211305 ]
  10. Carlsson A, Lindqvist M: Metatyrosine as a tool for selective protection of catecholamine stores against reserpine. Eur J Pharmacol. 1967 Dec;2(3):187-92. [PubMed:5590341 ]
  11. Blaschiko H, Longlands MG: Some observations on the bacterial decarboxylation of metatyrosine. Naunyn Schmiedebergs Arch Pharmacol. 1972;273(4):430-3. [PubMed:4262104 ]
  12. Anden NE, Fuxe K, Henning M: Mechanisms of noradrenaline and 5-hydroxytryptamine disappearance induced by alpha-methyl-dopa and alpha-methyl-metatyrosine. Eur J Pharmacol. 1969 Dec;8(3):302-9. [PubMed:5263681 ]
  13. Singh PP, Das PK: Role of catecholamines in the hypothermic activity of cannabis in albino rats. Psychopharmacology (Berl). 1976 Nov 10;50(2):199-204. [PubMed:826962 ]
  14. HAGEN P: Observations on the substrate specificity of DOPA decarboxylase from ox adrenal medulla, human phaeochromocytoma and human argentaffinoma. Br J Pharmacol Chemother. 1962 Feb;18:175-82. [PubMed:13903593 ]
  15. Gloge A, Langer B, Poppe L, Retey J: The behavior of substrate analogues and secondary deuterium isotope effects in the phenylalanine ammonia-lyase reaction. Arch Biochem Biophys. 1998 Nov 1;359(1):1-7. [PubMed:9799553 ]
  16. Sandler M, Corne SJ, Stephens R, Shaw DM, Hunter DR, Stern GM: Metatyrosine in the treatment of parkinsonism. Lancet. 1972 Sep 16;2(7777):605. [PubMed:4115783 ]